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4-Chlorobenzylamine → N-(4-Chlorobenzyl)-3,7-dimethyl-2-(morpholin-4-ylmethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

HRID 2307307
Notes
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Reaction equation

HRID 2307307 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[C:8]([C:12](OCC)=[O:13])=[CH:7][N:6]([CH3:17])[C:5]=2[S:4][C:3]=1[CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1>CO>[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH:31][C:12]([C:8]2[C:9](=[O:11])[C:10]3[C:2]([CH3:1])=[C:3]([CH2:18][N:19]4[CH2:20][CH2:21][O:22][CH2:23][CH2:24]4)[S:4][C:5]=3[N:6]([CH3:17])[CH:7]=2)=[O:13])=[CH:28][CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 22605733Ethyl 3,7-dimethyl-2-(morpholin-4-ylmethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate

Product 1

HCID 22605682N-(4-Chlorobenzyl)-3,7-dimethyl-2-(morpholin-4-ylmethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of ethyl 3,7-dimethyl-2-(morpholin-4-ylmethyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate (Preparation 28, 700 mg) and 4-chloro-benzylamine (1.25 mL) is heated to 190° C. under a nitrogen atmosphere for 1 h. The reaction mixture is allowed to cool briefly and methanol (10 mL) is added. After cooling to room temperature, the product is filtered and washed with methanol and diethyl ether to afford 634 mg of the title compound as a white solid. Physical characteristics. M.p. 222-224° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.67, 8.66, 7.41-7.33, 4.52, 3.92, 3.67, 3.59, 2.51, 2.47; MS (ESI+) m/z 446 (M+H)+. Anal. Found: C, 59.11; H, 5.47; N, 9.32; Cl, 7.96; S, 7.17.

Workup

  1. temperatureto cool briefly
  2. temperatureAfter cooling to room temperature
  3. filtrationthe product is filtered
  4. washwashed with methanol and diethyl ether

Sources & evidence

ORD record
ord-81f56b9743984273b5332a45bfabe381
Source dataset
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06831081B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes